Objective

To synthesize a Ugi product following the EXPLAN005 , using Methylamine , Tosylmethyl isocyanide, formic acid, and 2-methoxynaphthalene-1-carbaldehyde. The compound will contribute towards a library for Falcipain2 inhibitors.
This compunds was ranked 22 in the DEXP014-V1B file from D-EXP014 .The purpose of this experiment is to synthesize an anti-malarial compound based on the inhibition of falcipain-2, as described in this summary post.

Procedure

As described in Explan005

ID/ Lib Rank	Solvent	Aldehyde	Amine	Carboxylic Acid	Isocyanide	Ppt Yes/No
168-2/22	Methanol	2-methoxynaphthalene-1-carbaldehyde	methylamine, 2.0M solution in methanol.	formic acid	tosylmethyl isocyanide
Quantity	1000uL	0.5mmol, 93.105mg	0.5mmol, 19.78 ul (error)	0.5mmol, 18.86ul	0.5mmol, 97.62 mg

Density information found at the Ugi Chemicals page.

Results

5 min after mixing all components (Exp172A)

All results are recorded Master Table and Workflow Tables .

Discussion

Conclusion

Experiment aborted due to a miscalculation in the amount of methylamine. A total of 19.78ul were added to the solution where the proper amount is 250ul.

Log

2008-02-19

13:25 Added methanol to one dram vial
13:30 Added amine
13:31 Vortexed 15 seconds
13:46 Added aldehyde
13:47 Vortex 2 minutes
13:49 Added acid
13:50 Vortexed 15 seconds
14:04 Added isocyanide
14:06 Vortexed 20 seconds
14:11 Took picture 172A

Tags

Methylamine InChI=1/CH5N/c1-2/h2H2,1H3BAVYZALUXZFZLV-UHFFFAOYAN
Tosylmethyl isocyanide InChI=1/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3CFOAUYCPAUGDFF-UHFFFAOYAC
formic acid InChI=1/CH2O2/c2-1-3/h1H,(H,2,3)BDAGIHXWWSANSR-UHFFFAOYAT
2-methoxynaphthalene-1-carbaldehyde InChI=1/C12H10O2/c1-14-12-7-6-9-4-2-3-5-10(9)11(12)8-13/h2-8H,1H3 YIQGLTKAOHRZOL-UHFFFAOYANUgi ProductInChI=1/C23H24N2O5S/c1-16-8-11-18(12-9-16)31(28,29)14-24-23(27)22(25(2)15-26)21-19-7-5-4-6-17(19)10-13-20(21)30-3/h4-13,15,22H,14H2,1-3H3,(H,24,27) InChIKeyRDBIZMTYKUDBFZ-UHFFFAOYAM